I want this to not sound personal,
That's almost always a bad sign, like statements that start with "I don't mean to offend you, but..."
I expected this response, actually, and yeah, my skin's pretty tough so I don't mind at all. I understand it, and to a point I really do agree with you. It's where you start throwing around the 'should always' that we split off. Is the way you do things a good idea for many or most writers? I'd go so far as to say maybe-to-probably. But not all.
So, for example, SF stories should always go to F&SF and Asimov's first unless they explicitly violate something about the guidelines. Even if they're a longshot, you take the longshot no matter how much you think the story will be a perfect fit for On Spec, or Interzone or something.
Wouldn't it be great if there was a one-size-fits-all? But there's not.
A writer I greatly admire does it the way I do it. According to you, he's done it all wrong. He's published five novels, placed in prestigious comps like Bridport, Fish, won several first prizes, been in the Mississippi Review, The Atlantic's online Unbound thing when it came out, has a collection of shorts put out by a fairly prestigious literary press, etc. If the method or leveling up that he explained to me is good enough for him, I'm fine with it. It's working for me so far.
When I have a story that I know goes beyond what I've produced before, I do start at the top. But if I had to send every literary story to The New Yorker, Paris Review, Granta, The Atlantic and on down every time, I'd be one seriously tired and discouraged gal. Self-rejection is bad--sending a story to the lowest or no-paying places or the ones that take almost everything just so it's more likely to be picked up, instead of giving it a chance somewhere else. But it has to be tempered with a bit of realism. I personally think that if more brand new writers would start with their sights a little bit lower than the top of the mountain, they'd get further with less discouragement, grow faster as writers, and enjoy themselves a heck of a lot more on the way. But that's just my theory.
Another point against sending everything top tier and going down every time no madda wha is that I
enjoy writing for themed anthologies, themed issues, etc. Doing this gives me a writing rush--I like using prompts, working to a specific theme. I'm really pleased at some of places my writing has appeared, which in some cases I've written stories specifically
for, because I enjoy reading those places. They're solid print and online magazines I'm proud to be in, even if they don't pay a nickel a word or make Best Of lists. Do I feel like getting a story into an online zine that pays $10 is on a level with someone who got a story into Asimov's? No, of course not. However, regardless of what other people might think of it (which, let's be honest, most people know I'm not too concerned with), it can still be a point of pride for me. I can be happy about it, no matter who sneers or dismisses.
Despite your statements that "you must" (echo and thunder) do things your way, making absolute statements about what is and ought to be and what never happens for other people should probably be avoided. Except in cases of "if you've been chopping jalapenos, always wash your hands before you pee" and "never spit into the wind" and such, absolutes usually aren't.
I wish you the best in your writing career, I sincerely do. If your method works for, by all means keep doing it! I would never presume to say you must do it my way, because this great writer once gave me the advice I follow. When I reach the point where I even slightly suspect I'm producing stories of a high enough quality I'll probably start at the top every time, too. Until then, though, and I'm not saying this with a "bitchy" tone at all, just a slightly amazed one, who are you tell me I'm doing it all wrong? I don't even have any absolute way of doing it all the time even from story to story, let alone for every one.
You go your way, I'll go mine, we'll both enjoy our respective journeys, and I hope we shake hands up at the top somewhere.
Shelley